CA2074178A1 - Bleaching detergent composition - Google Patents
Bleaching detergent compositionInfo
- Publication number
- CA2074178A1 CA2074178A1 CA002074178A CA2074178A CA2074178A1 CA 2074178 A1 CA2074178 A1 CA 2074178A1 CA 002074178 A CA002074178 A CA 002074178A CA 2074178 A CA2074178 A CA 2074178A CA 2074178 A1 CA2074178 A1 CA 2074178A1
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- chain
- attached
- acyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims description 28
- 238000004061 bleaching Methods 0.000 title claims description 17
- 239000003599 detergent Substances 0.000 title claims description 12
- 125000002252 acyl group Chemical group 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 235000000346 sugar Nutrition 0.000 claims abstract description 28
- 150000002402 hexoses Chemical class 0.000 claims abstract description 10
- 150000002972 pentoses Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 25
- 238000005406 washing Methods 0.000 claims description 24
- -1 dedacanoyl Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- 150000001320 aldopentoses Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical group OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002401 hexose derivatives Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 2
- 208000007976 Ketosis Diseases 0.000 claims 2
- 150000002584 ketoses Chemical group 0.000 claims 2
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 claims 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
- 125000000704 aldohexosyl group Chemical group 0.000 claims 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 abstract description 11
- 235000020095 red wine Nutrition 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 5
- 235000015067 sauces Nutrition 0.000 abstract description 4
- 240000004178 Anthoxanthum odoratum Species 0.000 abstract description 2
- 240000004658 Medicago sativa Species 0.000 abstract description 2
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 239000012190 activator Substances 0.000 description 19
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 18
- 239000007844 bleaching agent Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- UAOKXEHOENRFMP-ZJIFWQFVSA-N [(2r,3r,4s,5r)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C=O UAOKXEHOENRFMP-ZJIFWQFVSA-N 0.000 description 14
- 244000025254 Cannabis sativa Species 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 241001122767 Theaceae Species 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 150000004965 peroxy acids Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000014101 wine Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229930182470 glycoside Natural products 0.000 description 4
- 240000004160 Capsicum annuum Species 0.000 description 3
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000001511 capsicum annuum Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 229940120146 EDTMP Drugs 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 2
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229940045872 sodium percarbonate Drugs 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- YIMYUGFRPUNGOM-UHFFFAOYSA-N 4-(3,5,5-trimethylhexanoyloxy)benzenesulfonic acid Chemical compound CC(C)(C)CC(C)CC(=O)OC1=CC=C(S(O)(=O)=O)C=C1 YIMYUGFRPUNGOM-UHFFFAOYSA-N 0.000 description 1
- 241000486634 Bena Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102100024342 Contactin-2 Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101000909516 Homo sapiens Contactin-2 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 125000001924 fatty-acyl group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002231 fructose derivatives Chemical class 0.000 description 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 150000002243 furanoses Chemical group 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002581 ketopentoses Chemical class 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 235000015113 tomato pastes and purées Nutrition 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 150000003741 xylose derivatives Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/391—Oxygen-containing compounds
- C11D3/3912—Oxygen-containing compounds derived from saccharides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3942—Inorganic per-compounds
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Abstract
Certain sugar derivatives have bleach-activating effect both on ''hydrophilic'' stains (e.g. tea or red wine) and on ''hydrophobic'' stains (e.g. grass or tomato sauce). The compounds in question are derivatives of pentoses or hexoses, having a long-chain acyl group and one or more short-chain acyl or aroyl groups attached through ester bonds. Optionally, a short-chain alkyl group is attached through a glycosidic bond. These compounds are non-toxic and biodegradable, and can conveniently be prepared by methods known in the art.
Description
WO 9]/10719 PCl'tDK91/00016 BL~ACHING DETERGENT COMPOSITION
~C~N!C ` L ,- 'LD
".is ,r,ven.,or; relatas to a blaaching detergent composition, to a washing and ~!~aching liquor, and to a washing and bleaching process. More 5 specifically, th^sa comprise a hydrogen peroxide source and a bleach activator.
The inventiGn ~i~o relatas to a compound for use as a bleach activator.
~ACKGP~Gu~iD i~sT
It is well known that detergents comprising peroxygen bleaches such as sodium perborate (PB) or sodium percarbonate (PC) are effective in removing 10 stains from textiles. It is also known that the bleaching effect at temperatures below 50 C can be increased by using a peracid precursor (bleach activator) such as tetraacetylethylenediamine (TAED), nonanoyloxybenzenesulfonate (NOBS, described in US 4,412,934), 3,5,5-trimethylhexanoyloxybenzenesulfonate (ISONOBS, describedin EP 120,591), or pentaacetylglucose (PAG), which is perhydrolyzed to form a 15 peracid as the active bleaching species, leading to improved bleaching effect.
EP 325,100 proposes use of an acetylated sugar ether containing a long-chain alkyl group as a bleach activator. However, such compounds cannot be easily prepared.
It is the object of the invention to provide use of an improved bleach 20 activator.
STATEMENT OF T~iE iNVEN~ON
'~Jz have surprisingly found that certain sugar derivatives have bleach-activating effac. both on "hydrophilic" stains (e.g. tea or red wine) and on "hydrophobic" stains (e,g. grass or tomato sauce). The compounds in question are WO 91/10719 PCI'/DK9~/00016 2~7~ 78 2 derivatives of pentoses or hexoses, havin~ r~ ~.in ?~c~JI group and one or more short-chain acyl or aroyl groups attach-d ~hrou~- s.-r bonds. Optionally, a short-chain alkyl ~roup is a::aC;~c~ ~ U~ ~ `: ~.` .~ ~^..,~` ~ ~~~'., ' .,^, ~, Jl~l~`J~Un ~a are non-toxic and biodegradable, and can convenientiy b prepared by methods 5 known in the art.
Ac_~rdingly, th~ ,r.~.!ar,tl~,,-. ;,rc,~ a~ Qn~si;~
comprising a scurca o, hydro;~-n" -~ C~rlTIU'_ (A-CO-) (R'-CO-wherein X is a pemose or nexose susar ,~oi~r~, A-CO is a lons-chai!l ~c~J! _r_u^. ~ Q!S~ ,A, -~ ^nQ C~ ~ ~Q .A'~ /in~
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CHzCH2~0)p-cH2 1 5 Ro(cH2-cH2-o) ROOC-CHzCH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q~ or RNHCO(CH2)r~
whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain ac~., or arc~;l s sup, R" is a C1-C4 alkyl group, yisOor 1, and n is 1, 2, 3 or 4, 30 whereby 3 2~7417g the alkyl group R (if prssent) is attached h ough a glycosidic bond to tha anomaric C a~ ; J
the acyl groups are attached through ester oonds.
It follows ;rom tho ~ m ~ .va !-a' ^~' groups in ~hC sugcr 5 molecule that n+y cannot axcacs ~ ,_r a r_-^.c_e _, _ - cr a hexcse Th o !n~a~ti~ ~ ? ` ~ r ~ A~ r? ii~ cr comprising a hydrogen p5rGXi~l5 ;70~1C5 al-l'~ C ':l~ao'~'c`aCSCn~Oa~l CVrl~POU~I~ cf formula (I), and a washing and bl~ac ing ~rceoss in .~ rosence ot these.
Further, the invention prG`i~u_S .^_`;_l _o",~c "ds Gf formula (I). One 10 aspect provides such compounds ;vherain n y is 3 or less These compounds are novel, whereas some hexose derivatives of formula (I) substituted at all OH gro :Jps (i.e. n+y=4) are known (e.g. JP-A 63-112,993).
Another aspect provides compounds of formula (I) wherein the long-chain acyl group excludes straight-chain saturated C8 and C12-C20 acyl and 15 wherein it is attached to the anomeric C atom. These compounds are novel and are particularly effective in the bleaching of hydrophobic stains.
DETAILED DESCRlPTlON OF lHE INyFNTION
Hvdroaen peroxide source The invention uses a hydrogen peroxide source as a bleaching agent, 20 i.e. a compound that provides hydrogen peroxide in an aqueous detergent solution. Examples are hydrogen peroxide itself, perborates such as sodium perborates and percarbonates such as sodium percarbonate.
Wo 91/107l9 PCrtDK91/00016 2 ~ 7 8 4 Suaar derivative The sugar derivatives according to the invention consist of a pentose or hexose sugar moie~, substituted with a long-chain acyl group and one or more short-chain acyl or aroyl groups through ester bonds, and optionally substitutedith a shor~-chain al'<yl sroup through a glycosidic bond.
Th~se sugar derivatives may be prepared by methods '~nown in Lhs art. ~eferer,ce .~ made to WO 89/01480; D. Piusquellec et al., Tetrahedron, `/ol. 42, vo. ~15~ 7 ~Q6; 1~ P!usquellec, Tetrahedron Letters, Vol. 28, No. 33, ?P
3809-3812, 1~,; J.i~/!. Williams et al., Tetrahedron, 1967, Vol. 23, pp. 136g-137~;
10 W.J. Hennen et al., J.Org.Chem., Vol. 53, pp. 4939-4945 (1988): A.H. Ilainss, Aav.
Carbohydr. Chem., Vcl. 33, pp. 11-51, 1976; K. Yoshimoto et al., Chem.Pharm.
Bull., 27 (11), 2661-2674 (1979); and Z. Gyorgydeàk et al., Liebigs Ann. Chem., 1987, pp. 23~-241. in cases where these methods lead to mixtures of isomers, these may, if so desired, be separated, e.g. by chromatography on silica gel.
The long-chain fatty acyl group may be saturated, mono- or poly-unsaturated; straight-chain or branched-chain, preferably C8-C18. Some preferredacyl groups are octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tetra-decanoyl, hexadecanoyl, octadecanoyl, 1 ~undecenoyl, oleoyl, 2-ethyl-hexanoyl and 3,5,~-trimethyl-hexanoyl. C8-C12 hydrocarbyl groups are particularly preferred as 20 they provide good bleach activation on hydrophobic stains.
The short-chain acyl or aroyl group is preferably a C2-C6 acyl group (especially acetyl) or benzoyl. Such derivatives can be prepared conveniently and economically.
The sugar moiety may be an aldohexose or aldopentose. For reasons 25 of economy, glucose or xylose derivatives are preferred.
Alternatively, the sugar moiety may be a ketohexose or ketopentose.
For reasons of economy, fructose derivatives are preferred.
In the case of glycoside esters (y=1), those with methyl or ethyl as the alkyl group R" may be preferrsd as they provide good surfactant properties.
30 The glycoside bond may be in the ~- or 13-anomeric form.
WO 91/10719 pcr/DK91/oool6 2~7'~ 7~
Amcng the sugar esters (y=0), compounds having one of the acyl-groups attached to the anomeric C-atom (the 1-position of an aldose or the 2-position cf e '~^se) ~rQ crsferred as they ars most rapidly psrhydrolyzQd. This acyl group may be in the ~- or ~-anomeric position. Sugar esters having a long-5 chain acyl glou~ (aa ;,paci,ied above) attached to ;h? anomeric C-atom are preferred, ~ .ne~! are particularly efficient for bleaching hydrophobic stains.
Alternatively, -~.2r eslers having a short-chain acyl group (e.g. an acetyl sro~p) ~tl?~chQd ro, '~ne ~nOrQriC ~- ~.tom !l~a\J be preferred, e~s thev ~re particularl~/ efficiQn~
fcr blaach;,ng n,~l3philic stains.
rhe sugar derivatives may be in the pyranose or furanose form 't .ol,û~,v, from the above that the number n y + 1 of acyl and alkyl substituents in ~he sugar molecule may vary from 2 up to 4 for a pentose or up to 5 for a hexose. Derivatives with only 2 or 3 substituents (n+y = 1 or 2) may be preferred as they are more hydrophilic than those more fully substituted and 15 are therefore more easily dissolved and may furthermore be more efficient as surfactants.
Alternatively, it may be preferred to use fully substituted compounds (n+y = 3 for a pentose or 4 for a hexose), as these provide the maximum amount of peracid.
Sugar derivatives with the long-chain acyl group attached to a side chain of the sugar molecule (i.e. to the ~position of glucose or the 1- or 6-position of fructose) may be preferred when a relatively slow release of the long-chain peracid is desired, so as to retain a surfactant effect, while short-chainperacid still may be formed rapidly by perhydrolysis in other positions of the 2~ molecule.
I o ensure good stability, the bleaching detergent composition of the invention will generally be provided in particulate form. Preferably, the sugar darivative cf fcr",ula (I) should be present in crystalline form, and for good crystallization it is preferable to use the sugar derivative in pure form rather than 2 ~ 7 8 6 a mixture of isomers. For compounds substitutod ~At ~ho anome!ic C atom this implies use of either the ~- or the ~-form r~th~r than 3 mi~.ura of tl~,ese.
Som~ ~rcforrc~ in acyl)-gluccse in ~- or ,B-form where the Icng-chain acyl is sne of the following:
5 octanoyl, nonanoyl, ~ecar,oy!, u.i___^n^~ ca, ey; ~ u,^__ca,.cyi, 8 trimethylhe,~anoyl cr 2-athyl, j j~
Bleachina detera~nt com~o ~lior~
Th ~ p ro,~ i d b . _ _ c, . _ . . _ ~ . . _ _ _ _ _ . _ _ . . . _ ~ i . i _ . _ ~ _ . i ~. _; i ;;LA ~ ~J r, ;LA
preferably mixed in a moiar ralio Ol l U`! ~5 -~ " Or~^-!i-.Ci'i 1:1 10 10:1.
The amount cf p3!0~ido b!e-c~ ~h^- -_m, _siLIcn ,;, pi_l^-âbiy ,-90% by weight, most preferabl~J 5-20% (as P~ monohyr'rate). The amount of bleach activator is preferably 2-90%, e.g. 2-~0%, especially ~-30% (percentages b~
weight).
Many of the sugar derivatives used in the invention are effective as 15 non-ionic surfactants. In addition, the composition of the invention may comprise other surfactants, e.g. of the non-ionic and/or anionic type. Examples of nonionics are alcohol ethoxylates (AE), nonylphenol ethoxylatss, alkyl polyglycosides (APG), and monoesters of carbohydrates (e.g. of free sugars or of glycosides). Examplesof anionics are linear alkylbenzene sulfonates (LAS), fatty alcohol sulfates, fatty 20 alcohol ether sulfates (AES), ~-olefin sulfor,atrs (AOS) and soaps.
Further, the composition of the invention may contain other conventional detergent ingredients such as suds-controlling agents, foaming boosters, chelating agents, ion exchangers, alkalis, builders, cobui!ders, otherbleaching agents, bleach stabilizers, fabric softeners, anti-redeposition agents, 25 enzymes, optical brightaners, anti-corrosicr, as_nts, f, a5l ar,cas, dya-stu,fs, blueing agents, formulation aids, fillers and water The composition of the in~/en~Jr may be prs~/idDd in liquid form 5r in powder or granular form, It may be isrrr_iatecl in anaiogy with the frama formulations for powder detergents given at p. 288 of J. Falbe: Surfactants in WO 91/10719 PCr/DK91/00016 7 2~74~ 78 Consumer Products. Theory, Technology and Aoolicatioil S~ringer-Verlag 1987 by replacing all or part (e.g. 50%) of the non-ionic surractan~ ~lith ester according to the invention.
Washina and bleachinq licucr The was~ing l,q~o, 5F ~ 1 ! ^? ^ ,~ ed '~y ~iss~'~;"~,s .~,~
above-described det_rgent in wr~-., c .,~.~ ".r,^a; e--~ can ~ avC^5 ar,.
dissolved separatelv. Tyoicallv, the .O~ ,, e~ ,on .uill v~ gi, the amount of the hy~rogen percxi!~e _o~ s,i, ~sr~eci-hJ 0.~
g/l (calculated as soaium perDorare morvnycra~e;, ar,~ amounr or ;ne sug2r 10 derivative will be 0.1-2.5 g/l, espec!al!y Washina and bleachina orocess The washing process of the invention is typically carried out with the above-described liquor at temperatures of 2~60 C for 10-60 minutes in a conventional washing machine.
Figs. 1 - 3 and 5 show bleach activation at varying concentrations of three different sugar derivatives according to the invention on three different soilings. Fig. 4 shows a similar comparison of three sugar derivatives accordingto the invention and two prior-art bleach activators. Details are given in Example 20 5.
EXAMPLES
The preparations of the susar d-r,vatives w6re gPnerally mixtures of the ~- and ,B-anomers. In all cases satisfactory ' H-NMR spectra were obtained for WO 91/10719 PCr/DK91/00016 2 ~ 7 ~ 8 the preparations. The preparations were all approximately 90% pure, but were dosed in the bleaching experiments as if 100% pure.
.~less otherNise stated, the inventive sugar derivatives were added to the various test-solutions as either methanol or ethanol solutions, while TAED, 5 PAG, ar,~ 'SONC~S were added directly. It has been checked that me~hanol/-ethanol at .~ ls attained by adding the sugar derivatives in this way have no influence in -he e~parimenis performed.
ECAMPI~ 1 This example is concerned with an examination of glucose ester and 10 glycoside ester preparations as activators for hydrogen peroxide in the bleachirig of test swatches soiled with tea, red wine, or grass.
The test swatches used were prepared by homogeneousiy soiling cotton cloth with tea, red wine, or grass juice, and then air-drying the soiled cioth overnight in the dark. The resulting material was stored in the dark at 4C (tea, red 15 wine) or below 0C (grass) for at least 2 weeks before cutting test swatches.The experiments were carried out as small-scale analogues of a Terg-o-tometer washing trial, i.e. isothermally in a series of beakers with concertedstirring (and alternating stirring direction). The soiled textile was loaded to 9 g/l washing liquor.
The washing liquor employed was a 50 mM sodium carbonate buffer at pH 10.5 with 0.4 g nonionic surfactanVI added (the preparation Berol 160 fromBerol Nobel was used, a C12-C14 fatty alcohol ethoxylate with an EO value of 6).The washir;g liquor was prepared from demineralized water.
Washing temperature was 40~C.
Duration: 30 min After washing, the swatches were rinsed thoroughly in tap water and then air-dried in the dark overnight.
WO91/]0719 PCT/DK91/ ~ 16 9 2 ~ 7 ~
E~/aluation of the bleaching effects was carried out by measuring the remission at 460 nm of unfiltered light, using a Datacolor Elrephometer 2000.
le 1 below, preparation 1 is 1-0-acetyl-6-0-octanoylglucose, while preparations 2 and 3 are 2-0-acetyl and 3-O-acetyl derivatives of ethyl 6-0-dacanoylsiu~,v,,~lc,nosld2, respecively.
Table 1 I Remission , at ~60 nm (%) ! Clean ~tile 85 15 1 ~ed wine Tea 0. Soiled, not ~ashed 46 50 43 1. Reference (washing liquor alone) 53 50 70 2. 10 mM H202 washing liquor 67 66 75 3. As 2 + 2 mM prepn. 1 75 74 81 4. As 2 + 2 mM prepn. 2 71 69 80 5. As 2 T 2 m~ prepn. 3 7l 70 79 30 ¦ 6. As 2 + 1 mM TAED 74 72 76 The activator TAED (tetraacetylethylenediamine) was used for a comparison and was dosed to 1 mM, since it possesses 2 perhydrolyzable acetyl groups Standard deviations were in all cases below 1 remission unit. The three sugar derivative preparations thus all show benefits compared to using Hz02 alone; all are superior to TAED in removing grass stains; and preparation 1 is superiGr to T~D sn tea and red wine as well.
WO91/10719 PCT/DX91/000~6 2~7~ 78 10 This example is e3n,C~r?~ r, ~ r ^~ r derivative preparations as activators for hydrogen peroxic~. The e:<perimental setup was as described in 'xamp ~n Tabl2 2 hvelo~,Y, ~r~ c,~ ",-preparation 5 is 2,3,4-~ri-O-~ceihJI-c-^-~ C~J.~ a~ . . . _ ,~. r_. e~i~vr.;, ~^i a.
âre 2,3-di-O-acetyl and ~,3,~-tri-(~ ?~ ?~ "
pyranoside, res,,iectively.
Tne sugar derivative r~re?~r~t~ s wer^- s^ise~ tc 2 mM excei~t 10 preparations 6 and 7 which ~ere -'o~e~ ,,- "^i-- ~-.,.e ,~ .vu,l~ c:â ;~,pârâ-tions 2 and 3 in Table 1. The results are sho~ n in Table 2.
Table 2 Remission at 460 nm (%) Clean textile 85 Red winel Tea ¦ Grass 0. Soiled, not washed ~ 46 ~ 50 43 1. Reference (washing liquor alone) 1 53 50 70 2. 10 mM H202 in washing liquor ¦ 67 64 74 3. As 2 + 2 mM prepn. 4 j 74 70 84 4. As 2 + 2 mM prepn. 5 ¦ 74 70 73 5. As 2 + 0.08% prepn. 6 , 74 69 78 35 6. As 2 + 0.08% prepn. 7 1 72 69 75 Wo 91/10719 P~/DK91/00016 11 207~ ~ 7~
Standard deviations are 3S in E~ample 1, er~d we may thus again conclude that all the preparations give significant benefits as activators at the level tested.
With the experimental setuo ,r,~ -.ors o 1-G--c~
~C~N!C ` L ,- 'LD
".is ,r,ven.,or; relatas to a blaaching detergent composition, to a washing and ~!~aching liquor, and to a washing and bleaching process. More 5 specifically, th^sa comprise a hydrogen peroxide source and a bleach activator.
The inventiGn ~i~o relatas to a compound for use as a bleach activator.
~ACKGP~Gu~iD i~sT
It is well known that detergents comprising peroxygen bleaches such as sodium perborate (PB) or sodium percarbonate (PC) are effective in removing 10 stains from textiles. It is also known that the bleaching effect at temperatures below 50 C can be increased by using a peracid precursor (bleach activator) such as tetraacetylethylenediamine (TAED), nonanoyloxybenzenesulfonate (NOBS, described in US 4,412,934), 3,5,5-trimethylhexanoyloxybenzenesulfonate (ISONOBS, describedin EP 120,591), or pentaacetylglucose (PAG), which is perhydrolyzed to form a 15 peracid as the active bleaching species, leading to improved bleaching effect.
EP 325,100 proposes use of an acetylated sugar ether containing a long-chain alkyl group as a bleach activator. However, such compounds cannot be easily prepared.
It is the object of the invention to provide use of an improved bleach 20 activator.
STATEMENT OF T~iE iNVEN~ON
'~Jz have surprisingly found that certain sugar derivatives have bleach-activating effac. both on "hydrophilic" stains (e.g. tea or red wine) and on "hydrophobic" stains (e,g. grass or tomato sauce). The compounds in question are WO 91/10719 PCI'/DK9~/00016 2~7~ 78 2 derivatives of pentoses or hexoses, havin~ r~ ~.in ?~c~JI group and one or more short-chain acyl or aroyl groups attach-d ~hrou~- s.-r bonds. Optionally, a short-chain alkyl ~roup is a::aC;~c~ ~ U~ ~ `: ~.` .~ ~^..,~` ~ ~~~'., ' .,^, ~, Jl~l~`J~Un ~a are non-toxic and biodegradable, and can convenientiy b prepared by methods 5 known in the art.
Ac_~rdingly, th~ ,r.~.!ar,tl~,,-. ;,rc,~ a~ Qn~si;~
comprising a scurca o, hydro;~-n" -~ C~rlTIU'_ (A-CO-) (R'-CO-wherein X is a pemose or nexose susar ,~oi~r~, A-CO is a lons-chai!l ~c~J! _r_u^. ~ Q!S~ ,A, -~ ^nQ C~ ~ ~Q .A'~ /in~
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CHzCH2~0)p-cH2 1 5 Ro(cH2-cH2-o) ROOC-CHzCH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q~ or RNHCO(CH2)r~
whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain ac~., or arc~;l s sup, R" is a C1-C4 alkyl group, yisOor 1, and n is 1, 2, 3 or 4, 30 whereby 3 2~7417g the alkyl group R (if prssent) is attached h ough a glycosidic bond to tha anomaric C a~ ; J
the acyl groups are attached through ester oonds.
It follows ;rom tho ~ m ~ .va !-a' ^~' groups in ~hC sugcr 5 molecule that n+y cannot axcacs ~ ,_r a r_-^.c_e _, _ - cr a hexcse Th o !n~a~ti~ ~ ? ` ~ r ~ A~ r? ii~ cr comprising a hydrogen p5rGXi~l5 ;70~1C5 al-l'~ C ':l~ao'~'c`aCSCn~Oa~l CVrl~POU~I~ cf formula (I), and a washing and bl~ac ing ~rceoss in .~ rosence ot these.
Further, the invention prG`i~u_S .^_`;_l _o",~c "ds Gf formula (I). One 10 aspect provides such compounds ;vherain n y is 3 or less These compounds are novel, whereas some hexose derivatives of formula (I) substituted at all OH gro :Jps (i.e. n+y=4) are known (e.g. JP-A 63-112,993).
Another aspect provides compounds of formula (I) wherein the long-chain acyl group excludes straight-chain saturated C8 and C12-C20 acyl and 15 wherein it is attached to the anomeric C atom. These compounds are novel and are particularly effective in the bleaching of hydrophobic stains.
DETAILED DESCRlPTlON OF lHE INyFNTION
Hvdroaen peroxide source The invention uses a hydrogen peroxide source as a bleaching agent, 20 i.e. a compound that provides hydrogen peroxide in an aqueous detergent solution. Examples are hydrogen peroxide itself, perborates such as sodium perborates and percarbonates such as sodium percarbonate.
Wo 91/107l9 PCrtDK91/00016 2 ~ 7 8 4 Suaar derivative The sugar derivatives according to the invention consist of a pentose or hexose sugar moie~, substituted with a long-chain acyl group and one or more short-chain acyl or aroyl groups through ester bonds, and optionally substitutedith a shor~-chain al'<yl sroup through a glycosidic bond.
Th~se sugar derivatives may be prepared by methods '~nown in Lhs art. ~eferer,ce .~ made to WO 89/01480; D. Piusquellec et al., Tetrahedron, `/ol. 42, vo. ~15~ 7 ~Q6; 1~ P!usquellec, Tetrahedron Letters, Vol. 28, No. 33, ?P
3809-3812, 1~,; J.i~/!. Williams et al., Tetrahedron, 1967, Vol. 23, pp. 136g-137~;
10 W.J. Hennen et al., J.Org.Chem., Vol. 53, pp. 4939-4945 (1988): A.H. Ilainss, Aav.
Carbohydr. Chem., Vcl. 33, pp. 11-51, 1976; K. Yoshimoto et al., Chem.Pharm.
Bull., 27 (11), 2661-2674 (1979); and Z. Gyorgydeàk et al., Liebigs Ann. Chem., 1987, pp. 23~-241. in cases where these methods lead to mixtures of isomers, these may, if so desired, be separated, e.g. by chromatography on silica gel.
The long-chain fatty acyl group may be saturated, mono- or poly-unsaturated; straight-chain or branched-chain, preferably C8-C18. Some preferredacyl groups are octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tetra-decanoyl, hexadecanoyl, octadecanoyl, 1 ~undecenoyl, oleoyl, 2-ethyl-hexanoyl and 3,5,~-trimethyl-hexanoyl. C8-C12 hydrocarbyl groups are particularly preferred as 20 they provide good bleach activation on hydrophobic stains.
The short-chain acyl or aroyl group is preferably a C2-C6 acyl group (especially acetyl) or benzoyl. Such derivatives can be prepared conveniently and economically.
The sugar moiety may be an aldohexose or aldopentose. For reasons 25 of economy, glucose or xylose derivatives are preferred.
Alternatively, the sugar moiety may be a ketohexose or ketopentose.
For reasons of economy, fructose derivatives are preferred.
In the case of glycoside esters (y=1), those with methyl or ethyl as the alkyl group R" may be preferrsd as they provide good surfactant properties.
30 The glycoside bond may be in the ~- or 13-anomeric form.
WO 91/10719 pcr/DK91/oool6 2~7'~ 7~
Amcng the sugar esters (y=0), compounds having one of the acyl-groups attached to the anomeric C-atom (the 1-position of an aldose or the 2-position cf e '~^se) ~rQ crsferred as they ars most rapidly psrhydrolyzQd. This acyl group may be in the ~- or ~-anomeric position. Sugar esters having a long-5 chain acyl glou~ (aa ;,paci,ied above) attached to ;h? anomeric C-atom are preferred, ~ .ne~! are particularly efficient for bleaching hydrophobic stains.
Alternatively, -~.2r eslers having a short-chain acyl group (e.g. an acetyl sro~p) ~tl?~chQd ro, '~ne ~nOrQriC ~- ~.tom !l~a\J be preferred, e~s thev ~re particularl~/ efficiQn~
fcr blaach;,ng n,~l3philic stains.
rhe sugar derivatives may be in the pyranose or furanose form 't .ol,û~,v, from the above that the number n y + 1 of acyl and alkyl substituents in ~he sugar molecule may vary from 2 up to 4 for a pentose or up to 5 for a hexose. Derivatives with only 2 or 3 substituents (n+y = 1 or 2) may be preferred as they are more hydrophilic than those more fully substituted and 15 are therefore more easily dissolved and may furthermore be more efficient as surfactants.
Alternatively, it may be preferred to use fully substituted compounds (n+y = 3 for a pentose or 4 for a hexose), as these provide the maximum amount of peracid.
Sugar derivatives with the long-chain acyl group attached to a side chain of the sugar molecule (i.e. to the ~position of glucose or the 1- or 6-position of fructose) may be preferred when a relatively slow release of the long-chain peracid is desired, so as to retain a surfactant effect, while short-chainperacid still may be formed rapidly by perhydrolysis in other positions of the 2~ molecule.
I o ensure good stability, the bleaching detergent composition of the invention will generally be provided in particulate form. Preferably, the sugar darivative cf fcr",ula (I) should be present in crystalline form, and for good crystallization it is preferable to use the sugar derivative in pure form rather than 2 ~ 7 8 6 a mixture of isomers. For compounds substitutod ~At ~ho anome!ic C atom this implies use of either the ~- or the ~-form r~th~r than 3 mi~.ura of tl~,ese.
Som~ ~rcforrc~ in acyl)-gluccse in ~- or ,B-form where the Icng-chain acyl is sne of the following:
5 octanoyl, nonanoyl, ~ecar,oy!, u.i___^n^~ ca, ey; ~ u,^__ca,.cyi, 8 trimethylhe,~anoyl cr 2-athyl, j j~
Bleachina detera~nt com~o ~lior~
Th ~ p ro,~ i d b . _ _ c, . _ . . _ ~ . . _ _ _ _ _ . _ _ . . . _ ~ i . i _ . _ ~ _ . i ~. _; i ;;LA ~ ~J r, ;LA
preferably mixed in a moiar ralio Ol l U`! ~5 -~ " Or~^-!i-.Ci'i 1:1 10 10:1.
The amount cf p3!0~ido b!e-c~ ~h^- -_m, _siLIcn ,;, pi_l^-âbiy ,-90% by weight, most preferabl~J 5-20% (as P~ monohyr'rate). The amount of bleach activator is preferably 2-90%, e.g. 2-~0%, especially ~-30% (percentages b~
weight).
Many of the sugar derivatives used in the invention are effective as 15 non-ionic surfactants. In addition, the composition of the invention may comprise other surfactants, e.g. of the non-ionic and/or anionic type. Examples of nonionics are alcohol ethoxylates (AE), nonylphenol ethoxylatss, alkyl polyglycosides (APG), and monoesters of carbohydrates (e.g. of free sugars or of glycosides). Examplesof anionics are linear alkylbenzene sulfonates (LAS), fatty alcohol sulfates, fatty 20 alcohol ether sulfates (AES), ~-olefin sulfor,atrs (AOS) and soaps.
Further, the composition of the invention may contain other conventional detergent ingredients such as suds-controlling agents, foaming boosters, chelating agents, ion exchangers, alkalis, builders, cobui!ders, otherbleaching agents, bleach stabilizers, fabric softeners, anti-redeposition agents, 25 enzymes, optical brightaners, anti-corrosicr, as_nts, f, a5l ar,cas, dya-stu,fs, blueing agents, formulation aids, fillers and water The composition of the in~/en~Jr may be prs~/idDd in liquid form 5r in powder or granular form, It may be isrrr_iatecl in anaiogy with the frama formulations for powder detergents given at p. 288 of J. Falbe: Surfactants in WO 91/10719 PCr/DK91/00016 7 2~74~ 78 Consumer Products. Theory, Technology and Aoolicatioil S~ringer-Verlag 1987 by replacing all or part (e.g. 50%) of the non-ionic surractan~ ~lith ester according to the invention.
Washina and bleachinq licucr The was~ing l,q~o, 5F ~ 1 ! ^? ^ ,~ ed '~y ~iss~'~;"~,s .~,~
above-described det_rgent in wr~-., c .,~.~ ".r,^a; e--~ can ~ avC^5 ar,.
dissolved separatelv. Tyoicallv, the .O~ ,, e~ ,on .uill v~ gi, the amount of the hy~rogen percxi!~e _o~ s,i, ~sr~eci-hJ 0.~
g/l (calculated as soaium perDorare morvnycra~e;, ar,~ amounr or ;ne sug2r 10 derivative will be 0.1-2.5 g/l, espec!al!y Washina and bleachina orocess The washing process of the invention is typically carried out with the above-described liquor at temperatures of 2~60 C for 10-60 minutes in a conventional washing machine.
Figs. 1 - 3 and 5 show bleach activation at varying concentrations of three different sugar derivatives according to the invention on three different soilings. Fig. 4 shows a similar comparison of three sugar derivatives accordingto the invention and two prior-art bleach activators. Details are given in Example 20 5.
EXAMPLES
The preparations of the susar d-r,vatives w6re gPnerally mixtures of the ~- and ,B-anomers. In all cases satisfactory ' H-NMR spectra were obtained for WO 91/10719 PCr/DK91/00016 2 ~ 7 ~ 8 the preparations. The preparations were all approximately 90% pure, but were dosed in the bleaching experiments as if 100% pure.
.~less otherNise stated, the inventive sugar derivatives were added to the various test-solutions as either methanol or ethanol solutions, while TAED, 5 PAG, ar,~ 'SONC~S were added directly. It has been checked that me~hanol/-ethanol at .~ ls attained by adding the sugar derivatives in this way have no influence in -he e~parimenis performed.
ECAMPI~ 1 This example is concerned with an examination of glucose ester and 10 glycoside ester preparations as activators for hydrogen peroxide in the bleachirig of test swatches soiled with tea, red wine, or grass.
The test swatches used were prepared by homogeneousiy soiling cotton cloth with tea, red wine, or grass juice, and then air-drying the soiled cioth overnight in the dark. The resulting material was stored in the dark at 4C (tea, red 15 wine) or below 0C (grass) for at least 2 weeks before cutting test swatches.The experiments were carried out as small-scale analogues of a Terg-o-tometer washing trial, i.e. isothermally in a series of beakers with concertedstirring (and alternating stirring direction). The soiled textile was loaded to 9 g/l washing liquor.
The washing liquor employed was a 50 mM sodium carbonate buffer at pH 10.5 with 0.4 g nonionic surfactanVI added (the preparation Berol 160 fromBerol Nobel was used, a C12-C14 fatty alcohol ethoxylate with an EO value of 6).The washir;g liquor was prepared from demineralized water.
Washing temperature was 40~C.
Duration: 30 min After washing, the swatches were rinsed thoroughly in tap water and then air-dried in the dark overnight.
WO91/]0719 PCT/DK91/ ~ 16 9 2 ~ 7 ~
E~/aluation of the bleaching effects was carried out by measuring the remission at 460 nm of unfiltered light, using a Datacolor Elrephometer 2000.
le 1 below, preparation 1 is 1-0-acetyl-6-0-octanoylglucose, while preparations 2 and 3 are 2-0-acetyl and 3-O-acetyl derivatives of ethyl 6-0-dacanoylsiu~,v,,~lc,nosld2, respecively.
Table 1 I Remission , at ~60 nm (%) ! Clean ~tile 85 15 1 ~ed wine Tea 0. Soiled, not ~ashed 46 50 43 1. Reference (washing liquor alone) 53 50 70 2. 10 mM H202 washing liquor 67 66 75 3. As 2 + 2 mM prepn. 1 75 74 81 4. As 2 + 2 mM prepn. 2 71 69 80 5. As 2 T 2 m~ prepn. 3 7l 70 79 30 ¦ 6. As 2 + 1 mM TAED 74 72 76 The activator TAED (tetraacetylethylenediamine) was used for a comparison and was dosed to 1 mM, since it possesses 2 perhydrolyzable acetyl groups Standard deviations were in all cases below 1 remission unit. The three sugar derivative preparations thus all show benefits compared to using Hz02 alone; all are superior to TAED in removing grass stains; and preparation 1 is superiGr to T~D sn tea and red wine as well.
WO91/10719 PCT/DX91/000~6 2~7~ 78 10 This example is e3n,C~r?~ r, ~ r ^~ r derivative preparations as activators for hydrogen peroxic~. The e:<perimental setup was as described in 'xamp ~n Tabl2 2 hvelo~,Y, ~r~ c,~ ",-preparation 5 is 2,3,4-~ri-O-~ceihJI-c-^-~ C~J.~ a~ . . . _ ,~. r_. e~i~vr.;, ~^i a.
âre 2,3-di-O-acetyl and ~,3,~-tri-(~ ?~ ?~ "
pyranoside, res,,iectively.
Tne sugar derivative r~re?~r~t~ s wer^- s^ise~ tc 2 mM excei~t 10 preparations 6 and 7 which ~ere -'o~e~ ,,- "^i-- ~-.,.e ,~ .vu,l~ c:â ;~,pârâ-tions 2 and 3 in Table 1. The results are sho~ n in Table 2.
Table 2 Remission at 460 nm (%) Clean textile 85 Red winel Tea ¦ Grass 0. Soiled, not washed ~ 46 ~ 50 43 1. Reference (washing liquor alone) 1 53 50 70 2. 10 mM H202 in washing liquor ¦ 67 64 74 3. As 2 + 2 mM prepn. 4 j 74 70 84 4. As 2 + 2 mM prepn. 5 ¦ 74 70 73 5. As 2 + 0.08% prepn. 6 , 74 69 78 35 6. As 2 + 0.08% prepn. 7 1 72 69 75 Wo 91/10719 P~/DK91/00016 11 207~ ~ 7~
Standard deviations are 3S in E~ample 1, er~d we may thus again conclude that all the preparations give significant benefits as activators at the level tested.
With the experimental setuo ,r,~ -.ors o 1-G--c~
6-O-acylglucosa ~Nith acyl = o^~n^y!, ~ ^.c~ c___a, _~ . :3..acecar~-y!, a,.-~
hexadecanoyl were tesled.
The following remissicn Yalu~s at 7~V n ~ re o'o.a,r.ec'.
Ref. C8 C10 C12 C14 C16 Red-wine swatches 66.5 74.7 74.8 74.3 72.6 72.6 Tea swatches 64.0 70.7 70.3 70.8 68.6 68.6 Grass swatches 73.7 81.1 &4.1 77.~ 66.7 5;~.G
The reference value, as in Example 1, was obtained with the washing liquor alone. Analogous bleaching trials with no backgrcund nonionic surfactant gave the following remission values at 460 nm (~O).
20 Ref. C8 C10 C12 C14 C16 Red-wine swatches 65.0 74.7 75.4 73.4 72.2 72.7 2~ Tea swatches 61.8 71.0 71.0 69.1 68.6 68.7 Grass swatches 47.9 63.3 83.~ 64.9 v4.8 ~1.6 WO 91/10719 PCr/DK91/000~6 2 ~7 ~ 7 12 Quite clearly, under both sets of conditions, there is an optimum stain removal at chain Isngth 10. With no nonionic present, all five inventive compounds provide bena.-.~s cn aac~ of thP three stains. With AE present, the same overallpicture is obtained for red-wine and tea stains as without AE, but the background e removal o, ~ra-s i_ so larg~ that only the C8 and C10 _empounds provide su~,-stantial furth~r r3r~0val (and the C14 and C1 6 compound even inter~ere , ,asativeiy ith the aicv, ~c, 3; ,oxylats).
lP~
!r~ ~.his e~ample the hydrogen peroxide activating effect of the full~J
10 acylated compound 1 ,2,3,4-tetra-O-acetyl-6-O-octanoylglucose (TAG-6-8, for short) was monitored by the amount of peracid formed in a model washing liquor (peracid formation may be monitored for example by iodometry at 5 C as described by Sully and Williams in Analvst, 1962, 67, 653).
The experimental conditions were: 10 mM H2O2 in 50 mM sodium 15 carbonate buffer (prepared from demineralized water) at pH 10.5 with 0.4 g nonionic surfac anVI added (the preparation Berol 160 from Berol Nobel was used,a C12-C14 fatty alcohol ethoxylate with an EO value of 6). TAG-6-8 was dosed to a level of 2 mM. The results are shown in Table 3:
T2ble 3 Time ~min) ¦ ~eracid ~m~) 3 1 3.0 2 . 7 __ The above data show that TAG-6-8 should be a very efficient activator for peroxide compounds since 3 mM peracid is formed in only 3 minutes from a 30 2 mM solution OT TAG-o-8.
WO 91/10719 PCr/DK91/00016 13 2~7'~ ' 7~
~tAMPI ~ 5 , ~e ~ cy!ated compounds TAG-6-8 = 1,2,3,4-tetra-0-acetyl-6-0-octanoylglucose and TAG-6-10, the corresponding decanoyl derivative, were subjec.ad Lo a ~;u..y o, e"ect versus increasing dosage, again under th_ small-scale washing c-rditicns described in Example 1. The hydrogen peroxide ccncentration ~,va~ .~opt ccnstant at 1 OmM while varying the activator concentration.
Fi9l_lrQs 1 ?'-'' " gr-rph the !ssu!ts. !ndeed, TAG-6-8, also presented in Example ~
,or its pe,-e,d ,o,,,,S~L,vn, ~laaches the hydrophobic as ~vell as the hydrophilic stains. Like ~,Yith the monoacetylated compounds in Example 3, the C8 and CtO
O compound~ "_. 3 b_have more or less identically on red-wine and tea stains, while the C10 compcund is clearly superior on grass.
For the compounds TAG-1-10 = 2,3,4,6-tetra-0-acetyl-1-0-decanoyl-glucose (as a preparation with more than 95% ~-anomer) and TAG-1-(10-undecenoyl)=2,3,4,0-tetra-O-acetyl-1-0-(1~undecenoyl)glucose (~:~ ratio approx 15 7:3) dose-effect studies analogous to the above ones are presented in Figures 3 and 5. It is seen that with the long-chain acyl placed at the anomeric carbon, an even better effect is obtained on the hydrophobic stain, i.e., grass, in comparison with the TAG-8 compounds, while maintaining significant effects on the hydrophilic stains. The two TAG-1 compounds behave very similarly.
Finally, in Figure 4 a comparison is made between the bleaching behavior on grass soiling of three of the TAG-fatty acyl compounds and the reference activator PAG (pentaacetylglucose), the most closely related compound within the prior art. it is seen that on this soiling, a signKicant improvement results from the substitution of one acetyl group by a long-chain acyl group, whether in2~ the 1- or the ô-position.
WO 91/10719 PfC~/DK91/00016 2 0f 7 f1~ ~7 8 14 This e~amp!r~ r~~
containing 2,3,4,6 tetra-O-acetyl-1-O-decanoylglf cose (T~G-1-,0), a derivative in accordance with the prescn. IllvcilAf;lv", /~i." hâ; _f a l~e .ivUv~ Cvn;âini.av sâCîl 5 of several prior art bleach 2C~i`/--i'C'`. ;-. -_-'i'_i~.- ^---: --.--''','.'.'ie`'^-!,r`.'!'`'`~'-",-zenesulfonate (!SONOBS), f -r.t a ac~ ;"i~i^a_~ a~ r--diamine (TAED~.
Th~ t~s. was ~,~r, iz~ v~ ,v~ . .;";_, .
contained 500 mls of a wash liauor et 40~D In ~:~/a~eir Cr l~ B,^-r:~ ne!c.r^~ 5^~
10 = 3:1). The wash liquGr cGntair, i~, f, J'~ '.'':''^. ~,I'`t S, - -f^-t^-,~, "t c~ v~i-.i comprising (in weight percent).
Linear Sodium C11 8 alkylbenzenesulfonate 5.9 Sodium Tallow alkyl sulfate 2.55 Sodium silicate (SiO2:Na2O = 1.6:1) 2.9 Magnesium sulfate 0.4 Polyacrylic acid 3.9 EDTA (ethylenediaminetetraacetic acid)0.25 CMC (carboxymethylcellulose) 0.3 EDTMP* 0.3 Sodium sulfate 10.7 Zeolite A 20.5 Dobanol 45E7 nonionic 5.4 Sodium carbonate 9.8 Suds suppressor 4.0 Sodium perborate tetrahydrate 20.0 Bleach activator 5 0**
* EDTMP = ethylenediaminetetrakis(metnylenephosphcnic acid) ** Except PAG which was 4.0 parts WO 91/10719 PCr/DK91/00016 2~7~ ~ 7~
Thus, the wash liquor ~,vas 1.0 ,~~ , as^q^t to PAG and TAG-1-10, and TAED and ISOi~C~S ,~ r~ ^i ,Jsi_ri amounts as TAG-1-10.
Tne wash iiquor ~,vas p,~ G,uiion of a,i of ~he 5 components axciq~,ct the pa,:Jc,a,~ .-cs,- ^~ ;n,o,. ~ ar5 a_~,ec as weighed amounts into the pG. i~lln^i~ r~_o".ri~,er,csd. ",5 ,,~
1-10 (as a r!q"~qt~ th q, into the pot conii~ining ihe ~ si~i .i ,~aoi ~ 9 ~ r~ _p~ Ti,v~
Each pot was lo~dGd ~,~lith a -5rj~ a; i-;r~ om-- ' .~`'', s~ tc, ~s sciled ~ ith 10 tea, wine, paprika and tomato stair,s. T,~ a a~ ;,.ains were used ,c evaluate hydrophilic stain bleaching and ~ 51_ Judged ins~.rumantally by a Hunter Colour Reflectance Meter. The paprika and tomato stains were used to assess hydrophobic stain removal and were assessed visually by an expert panel using a paired comparison technique. The panellists' preferences are expressed in Panel 15 Score Units (P.S.U.) on 1-5 Scheffe scale.
Results are shown below, normalised in each case to ISONOBS as 0. ISONOBS was chosen for this purpose as it generates a ~ater solubls peroxyacid bleach that has both hydrophiiic and hydrophobic stain removal capability. The figures in parentheses are the yardsticks at the 95% confidence 20 level.
DELTA L P.S.U.
Tea Wine Paprika Tomato PAG 1.6 (1.4) 0.5 (1 0) -1.8 (0.9) -3.6 (0.7) 25 TAED 2.8 (1.6) 0.7 (1.2j -1.6 (1.0) -4.0 (0.1) TAG-1-10 1.8 (1-9) 1.G (O G~ 0.~ ) 0.3 (0.6) WO 91/10719 PCl/DK91/00016 2~74~ ~8 16 It can be seen that, on hydrophilic stains, TAG-1-10 providas equivalent overall bleaching to PAG and TAED and, whilst not significantly better .h~n !SO~IO~S 3n ~ea stains, it is significantly better on wine stains. On hyc,G-phobic stains TAED and PAG give significantly poorer stain removal than iSONOBS
5 ~,vhilst TAG-,-1C is at laast as good as ISONOBS.
P~_- 7 -ihis example comoares the stain removal performance of TAG-1-10 (sae preca_~,"~s -Aample), pentaacetylglucose (PAG) and tetraacetylethylene-diamine (TAED) in a split bundle washing trial in domestic washing machines.
The test employed Miele (Model W756) Washing Machines employing 105 9 of a detergent product in a 60C mainwash cycle with 1 1 litres of water (city water of a hardness of approx. 12- dH). Each machine was loaded with 18.1 kg of normally soiled domestic fabrics (shirts, tea towels (dish towels), sheets, bath towels) together with swatches of technical stains representing greasy stains, 15 hydrophilic (bleachable) stains and hydrophobic stains. The greasy stains were lipstick, maka-up, boot-polish, eye-shadow, and dirty motor oil, all painted onto cotton and aged for two months. The hydrophilic (bleachable) stains were tea, wine, and coffee, all boiled onto cotton, and curry and blackberry, painted on and similarly aged. The hydrophobic stains, painted on and aged similarly, were ragu20 sauce, tomato paste and siciliana sauce. In addition a number of naturally soiled articles were split ito two halves,one of which was washed using the TAED-containing product while the other was washed in a product containing either PAGor TAG-1-10.
The detergent product had the following composition in weight 2~ percent.
17 2~ 7~
Linear Sodium C1 1 8 alkylbenzenesulfonate 6.9 Sodium Tallow alkyl sulfate 2.3 Dobonal ~'7 r~cnicnic 3.25 Tallow alcohoi ethoxylate 1.45 Sodium siliea.~ (SiO2:Na2O = 2:1) 3.~0 Sodium perberate tetrahydrate 18.25 ~cdium zec~ 22.3 CETPMP~ 0.20 Mlaleic anh~Jd,id3/acnJlic acid copolymer 3.50 Sodium carbonc,le 16.50 Trisodium c,trate 8.0 Optical brightener 0.2~
Carboxymethylcellulose 0.50 Suds suppressor 0.45 Moisture & miscellaneous 8.30 * DETPMP = diethylenetriaminepentakis(methylenephosphonic acid) 10~ 9 of the above product and a predetermined level of bleach activator were added to the machine using an Arielator~ dispensing device exceptin the case of the TAG-1-10 where the activator was predissolved in methanol and20 added via the detergent compartment of the dispenser drawer. In the washing liquor, the activator concentrations were 1.3mM (TAG-1-10), 1.3mM (PAG), and 2.0mM (TAED), respectively.
After washing the fabrics were dried in a rotary tumble dryer and the technical stain swatches and split items were assessed for stain removal by an 25 expert panel using a paired comparison technique.
The results are shown in Scheffe panel score units normalised to TAED = 0.
WO 91/10719 PCl'/DK91/00016 2~7~17~ 18 P.S.U.
Greasy 81eachable,Uyc,c-ncbicSplit itam TAED o ~ ^ n PAG -0.23 0.36 G._~ -0.08 5 TAG-1-10 0.67 0 ~ 0. ~7 It can ba saen ~hla~ .h~ '~CI^!-,~.C`I'I 'I.`~ .G-'~ ;^eacn activator demonstrates stain remcv21 be.r3i~s --crcs_ ?. `~ .,etv C~ "_.
hexadecanoyl were tesled.
The following remissicn Yalu~s at 7~V n ~ re o'o.a,r.ec'.
Ref. C8 C10 C12 C14 C16 Red-wine swatches 66.5 74.7 74.8 74.3 72.6 72.6 Tea swatches 64.0 70.7 70.3 70.8 68.6 68.6 Grass swatches 73.7 81.1 &4.1 77.~ 66.7 5;~.G
The reference value, as in Example 1, was obtained with the washing liquor alone. Analogous bleaching trials with no backgrcund nonionic surfactant gave the following remission values at 460 nm (~O).
20 Ref. C8 C10 C12 C14 C16 Red-wine swatches 65.0 74.7 75.4 73.4 72.2 72.7 2~ Tea swatches 61.8 71.0 71.0 69.1 68.6 68.7 Grass swatches 47.9 63.3 83.~ 64.9 v4.8 ~1.6 WO 91/10719 PCr/DK91/000~6 2 ~7 ~ 7 12 Quite clearly, under both sets of conditions, there is an optimum stain removal at chain Isngth 10. With no nonionic present, all five inventive compounds provide bena.-.~s cn aac~ of thP three stains. With AE present, the same overallpicture is obtained for red-wine and tea stains as without AE, but the background e removal o, ~ra-s i_ so larg~ that only the C8 and C10 _empounds provide su~,-stantial furth~r r3r~0val (and the C14 and C1 6 compound even inter~ere , ,asativeiy ith the aicv, ~c, 3; ,oxylats).
lP~
!r~ ~.his e~ample the hydrogen peroxide activating effect of the full~J
10 acylated compound 1 ,2,3,4-tetra-O-acetyl-6-O-octanoylglucose (TAG-6-8, for short) was monitored by the amount of peracid formed in a model washing liquor (peracid formation may be monitored for example by iodometry at 5 C as described by Sully and Williams in Analvst, 1962, 67, 653).
The experimental conditions were: 10 mM H2O2 in 50 mM sodium 15 carbonate buffer (prepared from demineralized water) at pH 10.5 with 0.4 g nonionic surfac anVI added (the preparation Berol 160 from Berol Nobel was used,a C12-C14 fatty alcohol ethoxylate with an EO value of 6). TAG-6-8 was dosed to a level of 2 mM. The results are shown in Table 3:
T2ble 3 Time ~min) ¦ ~eracid ~m~) 3 1 3.0 2 . 7 __ The above data show that TAG-6-8 should be a very efficient activator for peroxide compounds since 3 mM peracid is formed in only 3 minutes from a 30 2 mM solution OT TAG-o-8.
WO 91/10719 PCr/DK91/00016 13 2~7'~ ' 7~
~tAMPI ~ 5 , ~e ~ cy!ated compounds TAG-6-8 = 1,2,3,4-tetra-0-acetyl-6-0-octanoylglucose and TAG-6-10, the corresponding decanoyl derivative, were subjec.ad Lo a ~;u..y o, e"ect versus increasing dosage, again under th_ small-scale washing c-rditicns described in Example 1. The hydrogen peroxide ccncentration ~,va~ .~opt ccnstant at 1 OmM while varying the activator concentration.
Fi9l_lrQs 1 ?'-'' " gr-rph the !ssu!ts. !ndeed, TAG-6-8, also presented in Example ~
,or its pe,-e,d ,o,,,,S~L,vn, ~laaches the hydrophobic as ~vell as the hydrophilic stains. Like ~,Yith the monoacetylated compounds in Example 3, the C8 and CtO
O compound~ "_. 3 b_have more or less identically on red-wine and tea stains, while the C10 compcund is clearly superior on grass.
For the compounds TAG-1-10 = 2,3,4,6-tetra-0-acetyl-1-0-decanoyl-glucose (as a preparation with more than 95% ~-anomer) and TAG-1-(10-undecenoyl)=2,3,4,0-tetra-O-acetyl-1-0-(1~undecenoyl)glucose (~:~ ratio approx 15 7:3) dose-effect studies analogous to the above ones are presented in Figures 3 and 5. It is seen that with the long-chain acyl placed at the anomeric carbon, an even better effect is obtained on the hydrophobic stain, i.e., grass, in comparison with the TAG-8 compounds, while maintaining significant effects on the hydrophilic stains. The two TAG-1 compounds behave very similarly.
Finally, in Figure 4 a comparison is made between the bleaching behavior on grass soiling of three of the TAG-fatty acyl compounds and the reference activator PAG (pentaacetylglucose), the most closely related compound within the prior art. it is seen that on this soiling, a signKicant improvement results from the substitution of one acetyl group by a long-chain acyl group, whether in2~ the 1- or the ô-position.
WO 91/10719 PfC~/DK91/00016 2 0f 7 f1~ ~7 8 14 This e~amp!r~ r~~
containing 2,3,4,6 tetra-O-acetyl-1-O-decanoylglf cose (T~G-1-,0), a derivative in accordance with the prescn. IllvcilAf;lv", /~i." hâ; _f a l~e .ivUv~ Cvn;âini.av sâCîl 5 of several prior art bleach 2C~i`/--i'C'`. ;-. -_-'i'_i~.- ^---: --.--''','.'.'ie`'^-!,r`.'!'`'`~'-",-zenesulfonate (!SONOBS), f -r.t a ac~ ;"i~i^a_~ a~ r--diamine (TAED~.
Th~ t~s. was ~,~r, iz~ v~ ,v~ . .;";_, .
contained 500 mls of a wash liauor et 40~D In ~:~/a~eir Cr l~ B,^-r:~ ne!c.r^~ 5^~
10 = 3:1). The wash liquGr cGntair, i~, f, J'~ '.'':''^. ~,I'`t S, - -f^-t^-,~, "t c~ v~i-.i comprising (in weight percent).
Linear Sodium C11 8 alkylbenzenesulfonate 5.9 Sodium Tallow alkyl sulfate 2.55 Sodium silicate (SiO2:Na2O = 1.6:1) 2.9 Magnesium sulfate 0.4 Polyacrylic acid 3.9 EDTA (ethylenediaminetetraacetic acid)0.25 CMC (carboxymethylcellulose) 0.3 EDTMP* 0.3 Sodium sulfate 10.7 Zeolite A 20.5 Dobanol 45E7 nonionic 5.4 Sodium carbonate 9.8 Suds suppressor 4.0 Sodium perborate tetrahydrate 20.0 Bleach activator 5 0**
* EDTMP = ethylenediaminetetrakis(metnylenephosphcnic acid) ** Except PAG which was 4.0 parts WO 91/10719 PCr/DK91/00016 2~7~ ~ 7~
Thus, the wash liquor ~,vas 1.0 ,~~ , as^q^t to PAG and TAG-1-10, and TAED and ISOi~C~S ,~ r~ ^i ,Jsi_ri amounts as TAG-1-10.
Tne wash iiquor ~,vas p,~ G,uiion of a,i of ~he 5 components axciq~,ct the pa,:Jc,a,~ .-cs,- ^~ ;n,o,. ~ ar5 a_~,ec as weighed amounts into the pG. i~lln^i~ r~_o".ri~,er,csd. ",5 ,,~
1-10 (as a r!q"~qt~ th q, into the pot conii~ining ihe ~ si~i .i ,~aoi ~ 9 ~ r~ _p~ Ti,v~
Each pot was lo~dGd ~,~lith a -5rj~ a; i-;r~ om-- ' .~`'', s~ tc, ~s sciled ~ ith 10 tea, wine, paprika and tomato stair,s. T,~ a a~ ;,.ains were used ,c evaluate hydrophilic stain bleaching and ~ 51_ Judged ins~.rumantally by a Hunter Colour Reflectance Meter. The paprika and tomato stains were used to assess hydrophobic stain removal and were assessed visually by an expert panel using a paired comparison technique. The panellists' preferences are expressed in Panel 15 Score Units (P.S.U.) on 1-5 Scheffe scale.
Results are shown below, normalised in each case to ISONOBS as 0. ISONOBS was chosen for this purpose as it generates a ~ater solubls peroxyacid bleach that has both hydrophiiic and hydrophobic stain removal capability. The figures in parentheses are the yardsticks at the 95% confidence 20 level.
DELTA L P.S.U.
Tea Wine Paprika Tomato PAG 1.6 (1.4) 0.5 (1 0) -1.8 (0.9) -3.6 (0.7) 25 TAED 2.8 (1.6) 0.7 (1.2j -1.6 (1.0) -4.0 (0.1) TAG-1-10 1.8 (1-9) 1.G (O G~ 0.~ ) 0.3 (0.6) WO 91/10719 PCl/DK91/00016 2~74~ ~8 16 It can be seen that, on hydrophilic stains, TAG-1-10 providas equivalent overall bleaching to PAG and TAED and, whilst not significantly better .h~n !SO~IO~S 3n ~ea stains, it is significantly better on wine stains. On hyc,G-phobic stains TAED and PAG give significantly poorer stain removal than iSONOBS
5 ~,vhilst TAG-,-1C is at laast as good as ISONOBS.
P~_- 7 -ihis example comoares the stain removal performance of TAG-1-10 (sae preca_~,"~s -Aample), pentaacetylglucose (PAG) and tetraacetylethylene-diamine (TAED) in a split bundle washing trial in domestic washing machines.
The test employed Miele (Model W756) Washing Machines employing 105 9 of a detergent product in a 60C mainwash cycle with 1 1 litres of water (city water of a hardness of approx. 12- dH). Each machine was loaded with 18.1 kg of normally soiled domestic fabrics (shirts, tea towels (dish towels), sheets, bath towels) together with swatches of technical stains representing greasy stains, 15 hydrophilic (bleachable) stains and hydrophobic stains. The greasy stains were lipstick, maka-up, boot-polish, eye-shadow, and dirty motor oil, all painted onto cotton and aged for two months. The hydrophilic (bleachable) stains were tea, wine, and coffee, all boiled onto cotton, and curry and blackberry, painted on and similarly aged. The hydrophobic stains, painted on and aged similarly, were ragu20 sauce, tomato paste and siciliana sauce. In addition a number of naturally soiled articles were split ito two halves,one of which was washed using the TAED-containing product while the other was washed in a product containing either PAGor TAG-1-10.
The detergent product had the following composition in weight 2~ percent.
17 2~ 7~
Linear Sodium C1 1 8 alkylbenzenesulfonate 6.9 Sodium Tallow alkyl sulfate 2.3 Dobonal ~'7 r~cnicnic 3.25 Tallow alcohoi ethoxylate 1.45 Sodium siliea.~ (SiO2:Na2O = 2:1) 3.~0 Sodium perberate tetrahydrate 18.25 ~cdium zec~ 22.3 CETPMP~ 0.20 Mlaleic anh~Jd,id3/acnJlic acid copolymer 3.50 Sodium carbonc,le 16.50 Trisodium c,trate 8.0 Optical brightener 0.2~
Carboxymethylcellulose 0.50 Suds suppressor 0.45 Moisture & miscellaneous 8.30 * DETPMP = diethylenetriaminepentakis(methylenephosphonic acid) 10~ 9 of the above product and a predetermined level of bleach activator were added to the machine using an Arielator~ dispensing device exceptin the case of the TAG-1-10 where the activator was predissolved in methanol and20 added via the detergent compartment of the dispenser drawer. In the washing liquor, the activator concentrations were 1.3mM (TAG-1-10), 1.3mM (PAG), and 2.0mM (TAED), respectively.
After washing the fabrics were dried in a rotary tumble dryer and the technical stain swatches and split items were assessed for stain removal by an 25 expert panel using a paired comparison technique.
The results are shown in Scheffe panel score units normalised to TAED = 0.
WO 91/10719 PCl'/DK91/00016 2~7~17~ 18 P.S.U.
Greasy 81eachable,Uyc,c-ncbicSplit itam TAED o ~ ^ n PAG -0.23 0.36 G._~ -0.08 5 TAG-1-10 0.67 0 ~ 0. ~7 It can ba saen ~hla~ .h~ '~CI^!-,~.C`I'I 'I.`~ .G-'~ ;^eacn activator demonstrates stain remcv21 be.r3i~s --crcs_ ?. `~ .,etv C~ "_.
Claims (21)
1. A bleaching detergent composition comprising a source of hydrogen peroxide and a compound of the general formula (A-CO-) (R'-CO-)n X-R'y (I) wherein X is a pentose or hexose sugar moiety, A-CO is a long-chain acyl group, whereby A is one of the following:
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p ROOC-CH2CH2-, ROOC-CH=CH-, RCOO-CH2, RCONH(CH2)q- or RNHCO(CH2)r-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, R" is a C1-C4 alkyl group, y is 0 or 1, and n is 1, 2, 3 or 4, whereby the alkyl group (if present) is atTached through a glycosidic bond to the anomeric C atom, and the acyl groups are attached through ester bonds.
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p ROOC-CH2CH2-, ROOC-CH=CH-, RCOO-CH2, RCONH(CH2)q- or RNHCO(CH2)r-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, R" is a C1-C4 alkyl group, y is 0 or 1, and n is 1, 2, 3 or 4, whereby the alkyl group (if present) is atTached through a glycosidic bond to the anomeric C atom, and the acyl groups are attached through ester bonds.
2. A composition according to Claim 1, wherein X is an aldose, preferably xylose or glucose.
3. A composition according to Claim 1, wherein X is a ketose, preferably fructose.
4. A composition according to any of Claims 1 - 3, wherein A-CO is C8-C18 straight-chain, saturated acyl (preferably octanoyl, nonanoyl, decanoyl, undecanoyl, dedacanoyl, tetradecanoyl, hexadecanoyl, or octadecanoyl), C8-C18 straight-chain unsaturated acyl (preferably 10-undecenoyl or oleoyl) or C8-C18 branched-chain saturated acyl (preferably 2-ethyl-hexanoyl or 3,5,5-trimethyl-hexanoyl).
5. A composition according to any of Claims 1 - 4, wherein R'-CO is a C2-C6 acyl group (preferably acetyl) or benzoyl.
6. A composition according to any of Claims 1 - 5, wherein y=1, and R" is methyl or ethyl.
7. A composition according to any of Claims 1 - 5, wherein y=0 and one R'-CO is attached to the anomeric C atom.
8. A composition according to any of Claims 1 - 7, wherein n+y=1 or 2.
9. A composition according to any of Claims 1 - 7, wherein X is a pentose and n+y is 3, or X is a hexose and n+y is 4.
10. A composition according to any of Claims 1 - 9, wherein A-CO is attached to the 6-position of a hexose, the 5-position of an aldopentose or the 1-position of a ketose.
11. A composition according to any of Claims 1 - 9, wherein y = 0 and A-CO is attached to the anomoric C atom.
12. A composition according to any of claims 1 - 2 or 11, wherein X is an aldohexose, n is 2, and the R'-CO are attached in the 2- and 6-positions.
13. A composition according to any preceding claim, wherein the compound of formula (I) is present in crystalline form.
14. A composition according to any preceding claim, wherein the amount of hydrogen peroxide source is 1-90%, preferably 5-20% (percentage by weight, calculated as sodium perborate monohydrate), and the amount of said sugar derivative is 2-50%, preferably 5-30% (percentage by weight).
15. A particulate composition according to any preceding claim, wherein the molar ratio of the hydrogen peroxide source to the hexose derivative is from1:10 to 20:1, preferably from 1:1 to 10:1.
16. A washing and bleaching liquor containing a source of hydrogen peroxide, characterized by further comprising a compound as defined in any of Claims 1 -12.
17. A washing and bleaching process in the presence of a hydrogen peroxide source, characterized by the further presence of a compound as defined in any of Claims 1 - 12.
18. A compound of the general formula (A-CO-) (R'-CO-)n X -R"y (I) wherein X is a pentose or hexose sugar moiety, A-CO is a long-chain acyl group, whereby A is one of the following:
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p-, ROOC-CH2-CH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q- or RNHCO(CH2)r-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, R" is a C1-C4 alkyl group, y is 0 Gr 1, an n is 1, 2 or 3, whereby the alkyl group (if present) is attached through a glycosidic bond to the anomeric C, the acyl groups are attached through ester bonds, and n+y is 1, 2 or 3.
a C7-C19 straight-chain or branched, saturated or unsaturated hydrocarbyl, RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p-, ROOC-CH2-CH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q- or RNHCO(CH2)r-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, R" is a C1-C4 alkyl group, y is 0 Gr 1, an n is 1, 2 or 3, whereby the alkyl group (if present) is attached through a glycosidic bond to the anomeric C, the acyl groups are attached through ester bonds, and n+y is 1, 2 or 3.
19. A compound according to Claim 18, further characterized as in any of Claims 2 - 13.
20. A compound of the general Formula (A-CO-) (R'-CO-)n X (II) wherein X is a pentose or hexose sugar moiety, A-CO is a long-chain acyl group, whereby A is one of the following:
octyl, nenyl or decyl, a C7-C19 branched hydrocarbyl (saturated or unsaturated), a C7-C19 unsaturated hydrocarbyl (straight-chain or branched), RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p-, ROOC-CH2-CH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q- or RNHCO(CH2),-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, and n is 1, 2, 3 or 4, whereby the acyl groups are attached through ester bonds, and A-CO is attached to the anomeric C atom.
octyl, nenyl or decyl, a C7-C19 branched hydrocarbyl (saturated or unsaturated), a C7-C19 unsaturated hydrocarbyl (straight-chain or branched), RO(CH2-CH2-O)p-CH2-, RO(CH2-CH2-O)p-, ROOC-CH2-CH2-, ROOC-CH=CH-, RCOO-CH2-, RCONH(CH2)q- or RNHCO(CH2),-, whereby:
R is C8-C12 hydrocarbyl, p is 0, 1, 2 or 3, q is 1-5, r is 2-4, R'-CO is a C2-C7 short-chain acyl or aroyl group, and n is 1, 2, 3 or 4, whereby the acyl groups are attached through ester bonds, and A-CO is attached to the anomeric C atom.
21. A compound according to Claim 20, further characterized as in any of claims 2, 3, 5, 12 or 13.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK017290A DK17290D0 (en) | 1990-01-22 | 1990-01-22 | |
| DK0172/90 | 1990-01-22 | ||
| CN90104771.6A CN1027079C (en) | 1990-01-22 | 1990-07-16 | bleaching detergent composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2074178A1 true CA2074178A1 (en) | 1991-07-23 |
Family
ID=36763842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002074178A Abandoned CA2074178A1 (en) | 1990-01-22 | 1991-01-22 | Bleaching detergent composition |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0512031B1 (en) |
| JP (1) | JPH05504159A (en) |
| CN (3) | CN1027079C (en) |
| AR (1) | AR246305A1 (en) |
| AT (1) | ATE97692T1 (en) |
| AU (1) | AU659081B2 (en) |
| BR (1) | BR9105955A (en) |
| CA (1) | CA2074178A1 (en) |
| CS (1) | CS13791A2 (en) |
| DE (1) | DE69100685T2 (en) |
| DK (2) | DK17290D0 (en) |
| EG (1) | EG19321A (en) |
| ES (1) | ES2060364T3 (en) |
| IE (1) | IE910193A1 (en) |
| MA (1) | MA22047A1 (en) |
| NZ (1) | NZ236856A (en) |
| PT (1) | PT96542A (en) |
| WO (1) | WO1991010719A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5716569A (en) * | 1994-11-02 | 1998-02-10 | Hoechst Aktiengesellschaft | Granulated bleaching activators and their preparation |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9116939D0 (en) * | 1991-08-06 | 1991-09-18 | Unilever Plc | Bleach precursors and bleaching compositions |
| GB9122910D0 (en) * | 1991-10-29 | 1991-12-11 | Unilever Plc | Process for preparing sugar esters |
| WO1994016045A1 (en) * | 1993-01-18 | 1994-07-21 | Unilever N.V. | Machine dishwashing composition containing a corrosion inhibitor |
| JP3281445B2 (en) | 1993-04-28 | 2002-05-13 | 花王株式会社 | Fungicide composition |
| GB9423952D0 (en) * | 1994-11-24 | 1995-01-11 | Unilever Plc | Cleaning compositions and their use |
| DE19507668C2 (en) * | 1995-03-04 | 2000-01-27 | Suedzucker Ag | Detergent formulations containing an acylated disaccharide carboxylic acid |
| DE19510813A1 (en) * | 1995-03-24 | 1996-09-26 | Degussa | Activators for peroxo compounds and agents containing them |
| DE19641708A1 (en) * | 1996-10-10 | 1998-04-16 | Clariant Gmbh | Process for the preparation of a coated bleach activator granulate |
| US7041177B2 (en) | 2002-08-16 | 2006-05-09 | Ecolab Inc. | High temperature rapid soil removal method |
| WO2005100530A1 (en) * | 2004-04-16 | 2005-10-27 | Lg Household & Health Care Ltd. | Bleach activator comprising alkyloxy compound, manufacturing method thereof and bleaching composition containing the same |
| JP5328183B2 (en) * | 2008-03-17 | 2013-10-30 | 国立大学法人 長崎大学 | Method for producing glucoside ester derivative |
| BR112016010425B8 (en) | 2013-11-11 | 2023-01-31 | Ecolab Usa Inc | CONCENTRATED DETERGENT FOR WASHING UTENSILS AND ITS USE METHOD |
| US9890350B2 (en) | 2015-10-28 | 2018-02-13 | Ecolab Usa Inc. | Methods of using a soil release polymer in a neutral or low alkaline prewash |
| CN107698629B (en) * | 2017-10-19 | 2021-01-19 | 上海科技大学 | Disulfide bond bridging detergent and application thereof in membrane protein research |
| WO2019200294A1 (en) | 2018-04-13 | 2019-10-17 | Amtex Innovations Llc | Stitchbonded, washable nonwoven towels and method for making |
| US11884899B2 (en) | 2018-06-01 | 2024-01-30 | Amtex Innovations Llc | Methods of laundering stitchbonded nonwoven towels using a soil release polymer |
| US10822578B2 (en) | 2018-06-01 | 2020-11-03 | Amtex Innovations Llc | Methods of washing stitchbonded nonwoven towels using a soil release polymer |
| CA3100359A1 (en) | 2018-06-01 | 2019-12-05 | Amtex Innovations Llc | Methods of washing stitchbonded nonwoven towels using a soil release polymer |
| EP3918129B1 (en) | 2019-01-31 | 2024-04-24 | Ecolab USA Inc. | Controlling water levels and detergent concentration in a wash cycle |
| US12139842B2 (en) | 2019-01-31 | 2024-11-12 | Ecolab Usa Inc. | Rinse water reuse system and methods of use |
| CA3128194C (en) | 2019-01-31 | 2024-05-14 | Ecolab Usa Inc. | Controller for a rinse water reuse system and methods of use |
| WO2020160390A1 (en) | 2019-01-31 | 2020-08-06 | Ecolab Usa Inc. | Laundry machine kit to enable control of water levels, recirculation, and spray of chemistry |
| JP7417753B2 (en) | 2020-01-31 | 2024-01-18 | エコラボ ユーエスエー インコーポレイティド | Synergistic effect of amylase with oxygen bleach in clothing cleaning applications |
| US20220195341A1 (en) | 2020-12-23 | 2022-06-23 | Ecolab Usa Inc. | Soil removal on cotton via treatment in the rinse step for enhanced cleaning in the subsequent wash |
| WO2022140522A1 (en) | 2020-12-23 | 2022-06-30 | Ecolab Usa Inc. | Laundry sour softener with extra stability and additional benefits of laundry fire mitigation and sunscreen removal |
| EP4453162A1 (en) | 2021-12-22 | 2024-10-30 | Ecolab USA Inc. | Compositions comprising multiple charged cationic compounds for soil release |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK438887D0 (en) * | 1987-08-21 | 1987-08-21 | Novo Industri As | PROCEDURE FOR THE PREPARATION OF CHEMICAL COMPOUNDS |
| US4889651A (en) * | 1988-01-21 | 1989-12-26 | Colgate-Palmolive Company | Acetylated sugar ethers as bleach activators and detergency boosters |
| US4800038A (en) * | 1988-01-21 | 1989-01-24 | Colgate-Palmolive Company | Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners |
| DK27789D0 (en) * | 1989-01-23 | 1989-01-23 | Novo Industri As | DETERGENT - COMPOSITION |
-
1990
- 1990-01-22 DK DK017290A patent/DK17290D0/da unknown
- 1990-07-16 CN CN90104771.6A patent/CN1027079C/en not_active Expired - Fee Related
-
1991
- 1991-01-21 MA MA22320A patent/MA22047A1/en unknown
- 1991-01-21 IE IE019391A patent/IE910193A1/en unknown
- 1991-01-22 EP EP91903612A patent/EP0512031B1/en not_active Expired - Lifetime
- 1991-01-22 ES ES91903612T patent/ES2060364T3/en not_active Expired - Lifetime
- 1991-01-22 AT AT91903612T patent/ATE97692T1/en not_active IP Right Cessation
- 1991-01-22 EG EG3791A patent/EG19321A/en active
- 1991-01-22 DE DE91903612T patent/DE69100685T2/en not_active Expired - Fee Related
- 1991-01-22 CN CN91101115.3A patent/CN1030467C/en not_active Expired - Fee Related
- 1991-01-22 AR AR91318895A patent/AR246305A1/en active
- 1991-01-22 AU AU72141/91A patent/AU659081B2/en not_active Ceased
- 1991-01-22 JP JP3503673A patent/JPH05504159A/en active Pending
- 1991-01-22 DK DK91903612.9T patent/DK0512031T3/en active
- 1991-01-22 NZ NZ23685691A patent/NZ236856A/en unknown
- 1991-01-22 CA CA002074178A patent/CA2074178A1/en not_active Abandoned
- 1991-01-22 PT PT96542A patent/PT96542A/en not_active Application Discontinuation
- 1991-01-22 BR BR919105955A patent/BR9105955A/en unknown
- 1991-01-22 CS CS91137A patent/CS13791A2/en unknown
- 1991-01-22 WO PCT/DK1991/000016 patent/WO1991010719A1/en active IP Right Grant
-
1994
- 1994-05-24 CN CN94105123.4A patent/CN1102209A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5716569A (en) * | 1994-11-02 | 1998-02-10 | Hoechst Aktiengesellschaft | Granulated bleaching activators and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| MA22047A1 (en) | 1991-10-01 |
| CN1102209A (en) | 1995-05-03 |
| CN1055951A (en) | 1991-11-06 |
| CN1027079C (en) | 1994-12-21 |
| JPH05504159A (en) | 1993-07-01 |
| CS13791A2 (en) | 1991-08-13 |
| AU659081B2 (en) | 1995-05-11 |
| EP0512031B1 (en) | 1993-11-24 |
| AU7214191A (en) | 1991-08-05 |
| DE69100685T2 (en) | 1994-03-17 |
| DK17290D0 (en) | 1990-01-22 |
| BR9105955A (en) | 1992-11-10 |
| NZ236856A (en) | 1994-07-26 |
| WO1991010719A1 (en) | 1991-07-25 |
| IE910193A1 (en) | 1991-07-31 |
| EP0512031A1 (en) | 1992-11-11 |
| ATE97692T1 (en) | 1993-12-15 |
| ES2060364T3 (en) | 1994-11-16 |
| CN1058229A (en) | 1992-01-29 |
| DE69100685D1 (en) | 1994-01-05 |
| CN1030467C (en) | 1995-12-06 |
| DK0512031T3 (en) | 1994-04-18 |
| EG19321A (en) | 1995-06-29 |
| PT96542A (en) | 1991-11-29 |
| AR246305A1 (en) | 1994-07-29 |
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| EEER | Examination request | ||
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